The scope and limitations of three independent, though related routes leading to 5-substituted tetrahydroisoquinolines are explored: the Pictet-Spengler type cyclization of ortho-substituted 2-phenylethylamines, the Pomeranz-Fritsch type cyclization of meta-substituted benzylamines and the electrophilic trapping of 5-lithiated 4-lithiooxytetrahydroquinolines. The introduction of the substituent relies in all three cases on a neighboring group assisted, site selective metalation step. [on SciFinder (R)]
Title
Three complementary methods offering access to 5-substituted 1,2,3,4-tetrahydroisoquinolines
Published in
Tetrahedron
Volume
54
Issue
31
Pages
9023-9032
Date
1998
ISSN
0040-4020
Note
CAN 129:216547
28-8
Heterocyclic Compounds (More Than One Hetero Atom)
Institut de Chimie organique,Universite Batiment de Chimie,Lausanne-Dorigny,Switz.
Journal
written in English.
16414-34-9 (5-Bromo-3,4-dihydroxybenzaldehyde); 19522-96-4 (5-Bromopiperonal); 58343-42-3; 84087-59-2; 156634-90-1; 212332-80-4 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of tetrahydroisoquinolines); 81805-94-9P; 212332-74-6P; 212332-75-7P; 212332-76-8P; 212332-78-0P; 212332-79-1P; 212332-82-6P; 212332-84-8P; 212332-86-0P; 212332-88-2P; 212332-95-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of tetrahydroisoquinolines); 212332-77-9P; 212332-81-5P; 212332-90-6P; 212332-92-8P; 212332-94-0P; 212332-96-2P; 212332-97-3P; 212332-98-4P; 212332-99-5P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of tetrahydroisoquinolines)
Record creation date
2006-03-03
